Oxidation kinetics of an antiasthmatic, 2-[(4-hydroxyphenyl)amino]-5-methoxybenzenemethanol, and stabilization with ascorbic acid.
A novel antiasthmatic, 2-[(4-hydroxyphenyl)amino]-5-methoxybenzenemethanol (1), oxidizes to the corresponding iminoquinone in aqueous solutions. The reaction was monitored by a paired-ion reversed-phase HPLC method. The oxidation rate was highly dependent on the solution pH, with a large rate increase occurring above pH 6.1. In nonaqueous solution, the oxidation reaction was significantly slower. Ascorbic acid protects 1 from oxidation. The aqueous solution of the decomposed product is reduced to 1 in the presence of ascorbic acid.
Yu
A B
AB
Pharmaceutical Sciences, Sterling Drug, Inc., Rensselaer, NY 12144.
Portmann
G A
GA
D000627:Aminophenols / Q000737:chemistry*; D001205:Ascorbic Acid / Q000737:chemistry*; D001249:Asthma / Q000188:drug therapy*; D001592:Benzyl Alcohols / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D007773:Lactates / Q000737:chemistry; D010084:Oxidation-Reduction; D010710:Phosphates / Q000737:chemistry; D012996:Solutions; D013056:Spectrophotometry, Ultraviolet; D013447:Sulfites
D000627:Aminophenols; D001592:Benzyl Alcohols; D007773:Lactates; D010710:Phosphates; D012996:Solutions; D013447:Sulfites; C005200:sodium metabisulfite; C067148:2-((4-hydroxyphenyl)amino)-5-methoxybenzenemethanol; D001205:Ascorbic Acid